Triethylamine → Trans-(+)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-1H-indole-1-acetamide

HRID 649234Notes

Reaction equation

HRID 649234 reaction equation
C(N(CC)CC)C.[N:8]1([CH2:17][C:18]([OH:20])=O)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1.ClC(OCC)=O.[CH3:27][NH:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]1[N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>O1CCCC1>[CH3:27][N:28]([C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]1[N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)[C:18](=[O:20])[CH2:17][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 904481H-Indole-1-acetic acidHCID 13377463Cyclohexanamine, N-methyl-2-(1-pyrrolidinyl)-, trans-

Product 1

HCID 18607177Trans-(+)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-1H-indole-1-acetamideYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethylamine (139 μl, 1 mmol) was added to a solution of 1H-indole-1-acetic acid (175 mg, 1 mmol) in tetrahydrofuran (10 ml) at -15° C. with vigorous stirring. Ethyl chloroformate (96 μl, 1 mmol) was added, and the mixture stirred for five minutes. A solution of trans-(±)-N-methyl-2-(1-pyrrolidinyl)-cyclohexanamine (182 mg, 1 mmol) in tetrahydrofuran (2 ml) was added, and stirring continued for 30 minutes at -15° C., then 30 minutes at room temperature. The reaction was evaporated to small volume, the residue dissolved in ethyl acetate (50 ml), and washed with saturated sodium biocarbonate solution (3×50 ml). The organic extract was drige (MgSO4), evaporated under reduced pressure, and recrystallized from diethyl ether/methylene chloride to yield the amide (100 mg, 32%); Vmax C=0 1635 cm-1.

Workup

  1. stirringstirring
  2. waitcontinued for 30 minutes at -15° C.
  3. custom30 minutes
  4. customat room temperature
  5. customThe reaction was evaporated to small volume
  6. dissolutionthe residue dissolved in ethyl acetate (50 ml)
  7. washwashed with saturated sodium biocarbonate solution (3×50 ml)
  8. extractionThe organic extract
  9. customevaporated under reduced pressure
  10. customrecrystallized from diethyl ether/methylene chloride

Sources & evidence

ORD record
ord-76a2ce80eefb494fa86d0c5ef426a761
Source dataset
uspto-grants-1988_04
Patent number
US04738981

Reaction notes

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